


Bet You Didn't See That Coming

by RedQueenReigns



Series: Bet You Didn't See That Coming [1]
Category: Batman - All Media Types, DCU
Genre: Bruce Wayne is a Good Parent, Bruce Wayne is a Tired Dad, Bruce Wayne is exremely concerned about Tim, Crossdressing, Embarrassment, Jason Todd is an idiot, M/M, Never make a bet with Tim Drake, Rough Sex, The Batboys make a bet, Tim Drake is not having any of their shit, no beta we die like robins
Language: English
Status: Completed
Published: 2020-10-22
Updated: 2020-10-22
Packaged: 2021-03-08 23:53:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 7,832
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27154792
Author URL: https://archiveofourown.org/users/RedQueenReigns/pseuds/RedQueenReigns
Summary: Jason Todd doesn't always think before he speaks. He is well aware of this fault and so is everyone who knows him. He and the other Batboys make a bet with Tim that he can't pass as a girl at a high society function. Tim takes the bet is utterly determined to win. If he fails to do so, his face is going to be plastered across every paper in the country in disgrace. Of course, Tim has an ace up his sleeve that all but guarantees that he's going to win. And if Tim can manage to entice his long-time crush, then even better.
Relationships: Past Stephanie Brown/Tim Drake - Relationship, Tim Drake/Jason Todd
Series: Bet You Didn't See That Coming [1]
Series URL: https://archiveofourown.org/series/1982227
Comments: 20
Kudos: 334





	1. The Bet

**Notes for the Chapter:**

> I do not own DC Comics or anything associated with them, if I did I could afford not to work. The only thing I own is the female name Tim uses.

Jason had the tendency not to think before he spoke. He knew this, Tim knew this, hell, everyone who had ever met him knew this. But it still didn’t stop Jason from opening his big fat mouth.

The four boys had been spending the night in one of the media rooms, sprawled across the various couches and chairs, laughing and trading stories about their Robin years. Dick, Jason, and Tim were all bemoaning those missions that had required going undercover as a girl. Damian had been staring at them with a look that said he thought they were all insane. Jason thankfully hadn’t been forced into as many of those missions as Dick and Tim.

Jason, at twelve, had already been showing signs of the large bulk and blatant masculinity that Bruce also possessed. It made it very hard to mistake Jason, at any age, for a girl. Dick had managed it until he was sixteen at which point all his muscle and masculine genetics had made their abrupt appearance, taking him permanently out of those missions. Tim had been born with the unfortunate genetic disposition that made it very, very difficult to tell if Tim was a boy or a girl. It had caused Jason some confusion the first time he had met the kid, back when Jason was hell-bent on killing him. Unlike Dick and Jason, Tim had never grown out of his pretty. In fact, it had only gotten worse as he aged.

Granted, most of the time it was impossible to mistake Tim as anything other than male, with the way he dressed, spoke, and walked. But there were those moments where Jason was still mostly asleep, or really, really hungover and he really had to think about it for a second. Jason had never gone on a mission with Tim where Tim had to play the girl, for obvious reasons, and Jason didn’t think Dick had either. Damian looked far too much like his father to be able to take those kinds of missions, not to mention the Baby Bat was a little too stab happy to make it work. Bruce had never said anything about those missions, nor did Alfred and Jason had tried to get information out of both men.

Somehow, and Jason still wasn’t sure how they had gotten into an argument about whether Tim could still pull it off at seventeen or not. Almost everyone wagered on not. Tim had just shrugged and gone back to typing on his phone, not saying one way or the other.

This was the moment where Jason's big mouth opened and royally screwed them all.

Jason had needled Tim and wagered that Tim couldn’t pull it off and that he certainly couldn’t do it well enough to fool all of them. And that he especially couldn’t do it at a high society function. Tim had slowly looked up from his phone at that and Jason got the distinct feeling that he had just put his foot squarely in his mouth once more. The shining light of pure determination in Tim’s eyes did not reassure Jason.

“Challenge accepted.” Was all Tim said before returning to his phone once more.

They drifted off to bed a few hours later, well, Dick, Jason, and Damian went to bed. Tim left to go and do whatever it was insomniac Baby Birds did. Never the less Dick, Jason, and Damian all had chills running down their backs as they went to sleep that night. The next high society event was two weeks away, the annual Westscott Gala, Jason would have to get Bruce to make sure he was on the guestlist for it. As much as Jason despised those sorts of events he was willing to put up with all the bullshit just to watch Tim utterly fail. Jason honestly didn’t think Tim was going to be able to pull it off, no matter how confidant the little fuck was. Further, it would be fucking hilarious when Tim was called out in front of everyone and the scandal was splashed all across the front page of every newspaper in the country.

Later that night found Tim in the Batcave, digging through the truly extensive costume closet. Bruce had been standing behind Tim for five minutes now, still dressed in the Batsuit, minus the cape and cowl, watching as his second youngest son dug through their collection of evening gowns. Bruce was confused and not entirely sure if he wanted to ask. With Tim, this could be one of many things from Tim checking the stock to see if any needed to be changed out to having to find something for Stephanie or Cass. Bruce figured it was probably best if he just took the plunge and asked.

“What are you doing Tim?”

Tim turned to look at Bruce with a look of manic determination on his face that always made Bruce twitchy when it appeared on Tim's face. That look usually resulted in either utter humiliation for someone or copious amounts of pain.

“Jason challenged me,” Tim said.

Utter humiliation it was then. At least Bruce wasn’t going to be worrying about getting a call from one of his children that someone was bleeding profusely, or that they had all managed to break the exact same bone. Or in jail, that had been one of their more memorable nights.

“Do I want to know?” Bruce asked before he could stop himself.

Tim looked Bruce over for a long moment before thinking for an equally long moment.

That was the exact moment that Bruce officially washed his hands of the entire thing. Bruce did not like the fact that his son had more or less just looked him over like he was a piece of meat. Mostly because that was the look Bruce usually got from heiresses and models at events and galas. It absolutely should not have been coming from his seventeen-year-old son. So whatever the fuck Jason had just gotten himself into he was on his own. Bruce loved his children, he really did, but he was absolutely was not going to be taken down just because Jason decided to be a dumbass. Bruce could handle himself in any situation that might arise from this and right now that was all that mattered.

“Probably not. It'll play better if you don’t know.” Tim admitted. Yeah, that didn’t make Bruce feel any better.

Bruce cleared his throat awkwardly and shifted on his feet.

“Right, well, please don’t kill your brothers. I’ve no doubt that this, whatever this is, is all Dick, Jason, and Damian's fault.” With that blanket permission, Bruce turned on his heel and walked off with coffee mug in hand. He would let Alfred know that something was up and let him deal with it.

After that Tim promptly vanished from the manor and was only seen during nightly patrols. It gave everyone but Alfred a feeling of foreboding.


	2. The Gala

**Summary for the Chapter:**

> Tim debuts as a girl and makes everyone question their sexuality all in one blow.

_Two Weeks Later:_

“Okay, tell me again what is going on?” Stephanie Brown called through the door of Tim's ridiculously large and well-designed bathroom.

“Jason challenged me and now I have to utterly crush him or be humiliated and have my face splashed across every newspaper in the country for the next three months. Not that I'm going to lose.” Tim called back.

“Yeah, I got that. I meant, what was the challenge?” Stephanie asked.

At that moment the bathroom opened and Stephanie felt her mouth go dry and her heart skip a few beats.

“Oh my fucking God.” She squeaked out. 

Tim was dressed in a stunning white gown that appeared to be made of satin and had a small train. There was a large diamond-encrusted applique right about where Tim's lower stomach was. The sides from armpit to the tops of his hips were also encrusted with diamonds in a wide sideways triangle. There were two strips of wide satin that were just large enough to cover the fake A-cup breasts Tim was wearing. The gown had a very deep and wide V that went from the edges of his shoulders to just above his navel and would have greatly worried Stephanie had it not been for the rope after rope after rope of scarlet-colored pearls which connected the two strips of satin and entirely covered what would have otherwise been exposed skin, with only occasional peeks of white skin showing.

The pearls created a high neck on the gown before creating a very low scoop back on the back of the gown. The gown had barely any back and had the pearls not been there the gown would have probably been obscene rather than elegant with a vintage feel. The pearls were about the size of Bruce's thumbnails and somehow managed not to look gaudy. The entire outfit probably cost more than Stephanie would ever possibly make in her entire lifetime. The gown wasn’t tight to Tim's body after it reached his hips, but it didn’t flare out as a ballgown did. Rather it just laid there, emphasizing Tim's incredibly thin and muscled frame. 

Tim was also sporting a pair of scarlet-colored stiletto pumps that made Stephanie cringe when she looked at them. Tim had very little makeup on, just enough to soften what masculine edges he did possess and sharpen his cheekbones to give him an even more feminine look than he usually had. The makeup also highlighted the slight Asian lilt of his features and made his blue morning glory colored eyes pop. Beyond his eyes, the only spot of color on Tim's face was his scarlet painted lips. Tim had even applied professional-grade fake nails which were also painted scarlet and just pointed enough to give the mistaken impression that they couldn’t be used as weapons. Tim was also sporting a hell of a lot of extensions in his hair which was piled upon his head in an elegant, slightly vintage, up-do that Stephanie would never be able to mimic. 

Whatever magic Tim had used for this transformation had also hidden the multitude of scars that usually lined Tim’s arms, back, and face. Stephanie assumed that the high neck of the gown was to hide the large, thick scar on his throat, courtesy of Jason when he was all Pit crazy. Stephanie doubted there was anything but actual magic that would be able to hide that scar. She wondered if those hidden scars were still able to be felt or if they were non-existent now. She would have to ask.

Tim wasn’t wearing any jewelry beyond a simple pair of scarlet-colored ruby studs, probably because he was fucking dripping in pearls. Honestly, if Stephanie hadn’t been here when Tim went into the bathroom four hours ago, still looking like Tim, she would have had no idea that this was him. It was entirely unfair and Stephanie kinda wanted to punch him for it.

“What the fuck kind of challenge is this?” Stephanie managed to rasp out. 

“Jason, Dick, and Damian said I couldn’t still pass as a girl and that I couldn’t pass as one at a high society event. It was mostly Jason who made the wager, but Dick and Damian backed him up on it.”

“Well, you'll certainly be winning this bet. I mean, Jesus, boyfriend you look more like a girl than I do!” Stephanie said outraged now that the shock had passed. 

“Contour, Steph, contour.” Tim deadpanned.

“I think the better question is where the fuck you got that gown. I know for a damn fact that it wasn’t in the Cave.”

“Of course it wasn’t. I had it commissioned by a lady I know. I had Cass go in and be used for the measurements since she and I are the same size, more or less.” Tim didn’t need to say that the notable exception was the fact that Cass had breasts and Tim did not. Which meant that Tim's breast size was based on Cass'. Stephanie wasn’t sure how to feel about that. 

Stephanie looked Tim up and down before her brain stutter to a halt once more and she blinked. 

“Tim?” Stephanie asked. 

“Hmm?”

“Where's your dick?” 

Tim choked on his spit and his pale cheeks took on a faint dusting of red.

“Jesus, Steph! It's still there. There are ways to hide it. Modified jocks and the like.”

“That sounds incredibly uncomfortable,” Stephanie said thinking about the chest armor she wore with the Batgirl suit. 

“It's the male equivalent to a corset.” Stephanie grimaced at the thought. 

Stephanie watched as Tim crossed the room to reach the small vanity he had and pulled out a secret compartment full of various odds and ends that one might find in the room of a young woman. In this case, Tim pulled out a tiny bottle of perfume that most likely cost as much as Stephanie's college tuition. He dabbed a very small amount on each wrist and then rubbed his wrists together before dabbing an even smaller amount on each side of his neck. Whatever it was was very subtle and smelled slightly flowery. 

Stephanie wondered at the red accents and thought they might be because of his Red Robin persona. Until it clicked in her brain and she sucked in a sharp breath. Tim lightly turned to look at her with a raised brow. He grinned when he saw the look on her face.

“Holy shit! You’re totally trying to entice Jason with the red accents. That's Red Hood red!” 

“Yes, I am. Jason's point was to humiliate me but I intend to turn the tables on him with this. Of course, Dick and Damian will be joining him in his misery. Besides, there is no possible way that Jason won't be there tonight just to see what happens. And if the opportunity should arise that I could get close to Jason, then I would be foolish not to take it, now wouldn’t I?” Tim said with a predatory grin.

It wasn’t a secret between the two of them that Tim had the hots for Jason. Tim had been crushing on Jason since he was like ten. Jason's death had affected Tim far more than anyone had expected and his revival had brought a euphoric joy to Tim, only to have that diminish once Jason tried to kill him. But it hadn’t killed Tim's feelings for Jason. Once Jason had stopped trying to kill Tim and started working more with the Family, they got to know each other far better. So if the opportunity presented itself Tim was going to take it, even if it would result in a punch to the face from Jason when they were back at the manor.

The intercom buzzed at that moment and Tim stood. He glided over to the massive closet and shuffled through it for a few moments before coming back with a black coat that completely covered Tim’s gown, including the train. 

“Miss. Nychterida your escort for the evening is here.” Tim crossed to where the intercom was and hit the button to respond.

“Thank you, Lucas. I will be down momentarily.” Stephanie found herself gaping once again.

Tim’s voice had jumped up a few octaves and somehow turned itself into something smoky and sensual. Totally different from what Tim normally sounded like. She imagined that it helped that Tim’s voice was terribly deep, to begin with. 

“Well, I don’t know when I'll be back but you’re welcome to anything here or to call out for something. Please don’t burn my apartment down and yes I will tell you all the dirty details.” Tim said with a smile as he pulled his coat on and glided out the door.

“They are so fucked.” Stephanie said to the empty apartment with a mad grin.

Jason repressed the urge to tug on his shirt collar like some teenager. Jason had forgotten the level of dislike he held for these events and had this not been a potential gold mine of hilarity, Jason would never have come. As it was Jason was no longer as sure about his chances of winning as he had been at the beginning of the night. So far, Jason hadn’t spotted Tim and from the looks of alarm, Dick, and frustration, Damian, neither had the others. Bruce, on the other hand, was watching the three of them like a hawk and for once Jason couldn’t really blame him. 

Jason had marched up to Bruce's study the morning after he had issued the challenge to Tim and told Bruce to make sure he was on the guestlist for the Westscott Gala. The panicked and alarmed look on Bruce's face was entirely worth it. After that Jason had been subjected to Alfred's school for remedial manners. Luckily Dick and Damian were also drafted. Bruce was able to escape by running away to Wayne Enterprises for three days and never coming home. Jason assumed that Alfred had told Bruce what the challenge was because Bruce had been shooting all of them betrayed and horrified looks for three days now. 

Jason was trying to keep his eyes peeled for Tim, but it was hard since his eye, along with the eyes of every male in the room, kept being drawn back to the prettiest woman in the room. 

The woman had arrived about ten minutes after Bruce, Jason, Dick, and Damian. She had walked in on the arm of Congressman Mathers and the moment he had helped her out of her coat the entire room fell silent. She was wearing a stunning white gown of some kind of slightly shiny fabric, but the most eye-catching thing about it was that the woman's chest was draped in ropes of scarlet-colored pearls. Jason could see the occasional peak of pale flesh through the ropes. To make it even more enticing it was Red Hood scarlet. Her nails and lips had been painted in a matching shade. The woman was the envy of every woman in the room while Mathers was the envy of every male. Even Bruce looked like he nearly swallowed his tongue when he saw the woman.

The pair had walked up to their hosts for the night. Mr. Daniel Westscott and his wife Mrs. Marianne Westscott. Both had looked stunned and Mr. Westscott looked like he was about to have a heart condition when the woman smiled at him. Jason couldn’t hear what the congressman said, even if the room was near silent. Jason's eye kept being caught by all the red she was wearing and all the pale skin on display, making watching out for Tim a trying task. 

The woman hadn’t remained on the arm of the congressman long. She separated to begin mingling with the other guests and moved fluidly through them. She was pure grace and from the muscles in her back and general stature, she was quite fit too. Jason figured she was either a dancer or a model. Both required a person to be that kind of thin and pretty. The thing that Jason couldn’t figure was what the hell she was doing in a place like this. He was watching her pretty intently and everything she did was completely genuine. Her smiles were all real as was her laughter. None of it was faked. 

Bruce made a break for her the moment he could without appearing to be rude. Bruce scooped her up and took her out onto the dance floor. They danced for longer than was strictly appropriate for two strangers, but everyone knew better than to get between Bruce Wayne and whoever he was pursuing. There was a moment where Bruce went stiff as a board for a few seconds before relaxing. It was followed by Bruce's low chuckle suffusing through the room and the woman's low throaty chuckle right behind it. 

They danced for a few more songs before parting. Bruce melted into the crowd and the woman returned to mingling. It took another thirty minutes before she reached the corner where Jason, Dick, and Damian had retreated to look for Tim. She stopped near them and took a sip from the glass of champagne she was holding. She smiled after a few moments.

“Are you going to keep staring or introduce yourself?” Her voice was smoky with a sultry edge and lower than should have been attractive in a woman. It sent all the blood in Jason's body flowing south. From the way Dick shifted, he was also feeling the effects. 

Jason chose Damian to be the sacrificial lamb. He pushed the Demon Brat none too gently toward the woman and had to bite back his grin when the brat stumbled. The woman looked mildly surprised to see a small child and her smile turned into something far more child friendly.

“Hello, I wasn’t expecting there to be anyone younger than me here. Do you mind if I ask your name?” 

“D-Damian Wayne. Who are you?” Jason gaped at the Demon Brat. The little shit had actually stuttered and he was blushing. Jason and Dick exchanged wide-eyed looks.

“I'm Andromache Nychterida. It is a pleasure to meet you, Mr. Wayne.”

God, even her name sounded hot.

“Greek,” Damian stated with a slight furrow of his brows. 

Andromache hummed in slight surprise and some amusement. 

“Do you speak Greek, Mr. Wayne?” She asked.

“No. That is not one of the languages I speak.”

“Perhaps you would be willing to tell me what languages you do speak during a dance?” She didn’t give Damian the chance to protest as she dragged him off to the dance floor.

Jason and Dick could only watch in stunned disbelief as Damian attempted to dance with the most beautiful woman in the room. How were they supposed to find Tim if they were being distracted by beautiful women? Jason refused to lose this challenge to Tim. The little shit would more than likely be hiding in some corner somewhere, but they had already looked through all the corners before the woman arrived and then after her arrival. There was no sign of Tim at all. That meant that Tim was actually somewhere among the other guests and that he was winning. 

Somewhere during the time that Damian had been dragged onto the dance floor and Jason's mental freakout, Bruce had saddled over to stand next to them. 

“She's beautiful, isn’t she?” Bruce asked softly. 

Jason and Dick mutely nodded, because what the hell else could they say. 

“She's not here _with_ the congressman if you’re wondering. She's a model out of Greece and friends with the man's daughter. He needed an escort for the night and she needed to make connections. She had received an invite from someone else but the congressman didn’t like the idea of his daughter's friend going with some stranger, so he brought her.” Bruce explained. 

“Why are you out there hoarding her attention then?” Jason asked. 

“Because she's eighteen,” Bruce said with a look thrown at Jason that said he was treading on questionable ground. 

“That might have been acceptable when I was in my twenties, but I'm in my forties now. Dancing with her for a few songs is all I'm willing to do.” Bruce didn’t need to say that she was far too close in age to the good majority of Bruce's children for Jason to understand why Bruce did not chase after her.

“That said. She does make me wish I was a young man again.”

“Ew Bruce,” Jason said with a grimace that had Bruce chuckling.

“Ah, Mr. Wayne, come for another dance?” Andromache asked as she suddenly reappeared with a red-faced Damian who was looking anywhere but at Andromache and hunched in on himself. 

“I'm afraid not. The crowd might lynch me if I took up too much more of your time. I just came to retrieve my youngest son and speak to my other sons.” 

“Oh, I didn’t realize these other two handsome men were your sons as well. Damian was a dead giveaway, he looks just like you Mr. Wayne. If you don’t mind my asking, who is Damian's mother?” That question had all three boys stiffening. 

“Damian's mother and I didn’t work out, unfortunately. I was unaware that she was pregnant with Damian when we parted ways and didn’t know I had a son until ten years later when she finally told me.” 

“Oh, I'm sorry to hear that things didn’t work out between you two, but I'm glad that Damian has you now.” Once again every single bit of what she had just said was completely genuine. It was baffling to Jason. 

“Allow me to introduce my other children. This is my oldest, Dick Grayson, he's a police officer in Bludhaven. This is my second oldest, Jason Todd, he works in private security. I have a third son, Timothy Drake, he runs the business for me. And you already know Dami.” Jason fought the urge to cringe. Brucie was out in full force and he always freaked Jason way the fuck out. 

“It's wonderful to meet you all. I’ll admit I don’t follow the papers or magazines, too much about a model's life, so I don’t know much about you.” She said with a smile. 

“I'd love to stay and chat but I need to get Dami home and into bed. Boy's will you be alright finding your way home or do you want me to send Alfred to get you?” 

“I'll find my way home.” Jason and Dick both said at the same time. Andromache chuckled lightly. 

“Goodnight Mr. Wayne. It was a pleasure to meet you and your son. Damian, I enjoyed our dance.” 

Bruce gave a similar goodbye and hustled Damian away fairly quickly. Given the way Damian was hiding behind Bruce and hunching in on himself, Jason was able to suss out that reason fairly quickly. Poor Damian, this was a horrible place to suddenly be thrust into puberty. Though Jason figured there were far worse people Damian could be triggered by. Jason had ended up triggered by Dick, but that wasn’t all that surprising since the man was like walking fucking sex. 

The rest of the evening passed with Jason and Dick dancing on and off with Andromache. They also talked and got to know each other quite well. Jason definitely shot Dick a smug look when it became clear that Andromache was more interested in Jason than Dick. Dick took it well and made his own exit shortly after. Dick invited Andromache to visit them at the manor when she had the time between jobs. They had all truly enjoyed their time with Andromache and would like to spend more time with her outside stuffy parties. Dick and Andromache exchanged numbers and she promised to keep in touch and send pictures of where she traveled. 

Andromache vanished for a few songs to dance with the congressman she had arrived with before returning to Jason's side. 

“I've told Mr. Mathers that I’ve found other accommodation for the night. Would you like to take this somewhere more...private?” Andromache's voice was purring and she lightly traced one scarlet painted nail up Jason's side. 

Jason shuddered and moved even closer. 

“I would like that very much,” Jason answered. 

“Lead the way, Mr. Todd.” She smiled and took Jason's hand as he gently led her through the crowd. 

Jason ignored the glares from the males in the room and gently pulled her through a side door that led to the stairwell. The moment the door was shut and locked Jason pushed Andromache up against the wall and glued his mouth to hers. Andromache moaned into Jason's mouth and tangled her tongue with his as Jason's hands locked onto her hips. 

“Fuck, you’re beautiful.” Jason moaned as his hands wandered down her sides and hips. 

Jason grabbed fistfuls of her gown and pulled it up as much as he could and pressed himself flush against her. Jason rolled his hips into her and promptly froze. 

The chuckle this time was much lower and Jason felt instant panic race through him.

“Hello, Jason.” 


	3. Journey's End.

Jason ripped himself away with wide eyes. He watched as before his eyes the woman shifted into a languid slouch that only Tim seemed to be able to achieve. Her eyes turned calculating and the smile turned into a smirk. To make it even worse the boner Jason was sporting wasn’t going anywhere. In fact, it had twitched in an alarming fashion once it was revealed that Andromache was Tim. Well, fuck, Jason had absolutely lost this wager and he would admit it hands down. 

“Jesus fuck Babybird.” Jason rasped out. 

“The ball's in your court now, Jason. We can leave this here or keep going, either is fine.” Tim said with a shrug.

Either way was not fine. 

If Tim was telling him this it was because he wanted it and had pulled up all the courage he had to tell Jason that. Jason had no idea that Tim was interested in him like that. Why the hell would he be? Jason had tried and nearly succeeded, in killing him. It wasn’t like Jason wasn’t interested, his boner clearly showed that, and he was never going to be able to look at Tim and not see how hot of a girl he made. 

Apparently Jason had taken too long to say anything because Tim’s face shuttered and went blank. 

“Understood. Enjoy the rest of your evening Jason.” Tim said. Tim glided past with only the click of his heels to announce his presence.

Jason moved without thinking. His hand shot out and gently grabbed Tim's arm as he passed, keeping in mind how much stronger than Tim Jason was. He lifted Tim and shoved him less gently than before against the cinder block wall. Tim let out a small oomph as his back hit the wall and he couldn’t help but arch at the slightly rough treatment. Jason blinked and then smirked at Tim. He could absolutely provide that for Tim. 

“You're not going anywhere Babybird. If you want this then tell me right now and if you want to stop at any point you tell me and I will.” Jason whispered.

Tim sucked in a sharp breath and stared at Jason. 

“Do you mean that? Cause if you’re fucking with me right now Jason I'm going to stab you with my shoe.” Jason knew that was not an empty threat. 

“I meant every word Babybird.” 

“Then I want this. I want this more than anything in the world.” Tim breathed locking eyes with Jason. 

Jason lunged forward and shoved his tongue down Tim's throat. Tim moaned and rolled his hips against Jason's before making a frustrated sound. Jason smirked, he knew exactly what was frustrating Tim and Jason intended to drive Tim insane before he finally released him. At least that was the hope, but with the way Tim was grinding and writhing against him, Jason wasn’t entirely sure how realistic that goal was going to be. Already Jason was bucking against Tim in return and his gut was tightening. 

Yeah, Jason was way too wound up to take this as slow as he would like. All of a sudden Jason was against the wall and Tim was kneeling in front of him in a cloud of settling satin. Tim looked up at him from under his lashes and Jason made a whimpering groan that had Tim smiling. Jason didn’t stop Tim from reaching forward and unbuckling his belt and undoing his pants. Jason was the one to work them and his black boxer briefs off his hips just enough to expose his straining erection. 

Tim stared at him for a few seconds and Jason let him. Jason was by no means small, he had been blessed with both length and girth. For a split second, Jason was worried that Tim was scared by his size. That thought promptly vaporized as Tim licked his lips hungrily and stared at Jason like he was the best fucking thing Tim had ever seen. This time the sound Jason let out was a full-on whimper. No one had ever looked at Jason like that before and Jason wasn’t going to be able to close his eyes for months without seeing that look on Tim's face. 

Just the idea of Tim taking him between those scarlet painted lips was enough to bring Jason dangerously close to snapping. Jason closed his eyes and leaned his head back against the wall so he didn’t blow his load early. However, Jason's eyes snapped open and his back arched almost violently as Tim swallowed Jason all the way down in one solid go.

“Fuck!” Jason bellowed. 

Jesus, did Tim even have a fucking gag reflex? Furthermore, who the fuck taught him how to blow someone because Jason either wanted to kiss them or punch them. Jason couldn’t stop himself as he thrust his hips, pushing himself even further down Tim's throat. Tim moaned around Jason and drew back, lightly scraping his teeth along the length of Jason. Jason was panting harshly and had his hands fisted to keep himself from thrusting again. He didn’t want to hurt Tim.

Jason shuddered as Tim's long nails scraped along the column of Jason's thighs. 

“It's alright, Jason. You won't hurt me. I trust you.” Tim whispered. 

“Babybird.” Jason panted in a warning. Jason had just enough brain cells left to remember that he couldn’t call Tim by his name in case someone heard him. 

“You won't hurt me and if you did something I didn’t like I could stop you,” Tim reassured. 

“That's not...” Jason never finished because Tim chose that moment to slowly, inch by agonizing inch, swallow Jason back down until his nose touched skin. Jason could feel every inch of Tim’s throat and how deep down he was. That was enough and Jason's control snapped. 

Jason grabbed Tim by the hair and started fucking his mouth and throat like he was going to die if he didn’t. Tim moaned around Jason and one of Tim's hands snaked under the skirt of his gown and Tim began rubbing himself through the modified jock. Jason felt the string in his gut snap and Jason grabbed Tim by the back of his neck and pressed as far down as Tim's throat as he could and released. Tim swallowed all of it with the filthiest moan that Jason had ever heard. Carefully and gently Jason pulled himself out of Tim's throat. 

Tim was panting harshly and looking painfully frustrated. 

“Fucking shit Babybird.” Jason panted as he tried to get his brain to think again. Tim licking those red lips didn’t help.

The only thing keeping Jason upright at this moment was the wall behind him. Tim was still panting like he'd just sprinted across Gotham and was leaning his forehead against one of Jason's thighs. One of Jason's hands was gently patting Tim's hair since there were too many pins to actually stroke through the locks. However, the style was slightly disheveled, giving evidence of what they had been doing. It made Tim look all the hotter. 

“You alright?” Jason managed to get out. 

“Better than,” Tim answered, sounding like he had just gargled rocks. Jason winced slightly.

“I hope you’re up for another round because I am painfully hard and if you don’t fuck me I'm going to explode,” Tim said and Jason's breath caught in his throat. 

“Where do you want to go?” Jason immediately asked. 

“I've got a place near here,” Tim answered getting to his feet. 

Jason pushed off the wall and pulled his pants and boxer briefs back up and fastened them. Tim on the other hand was on the phone. Jason couldn’t hear what was being said but figured Tim was warning whoever to vacate the premises. Tim clicked the phone off and slipped it back inside the dainty looking clutch he was carrying. Tim smiled at Jason and Jason felt his cock twitch in his pants at the sight. Tim's lipstick had smeared ever so slightly at one corner of his mouth and fuck did Jason want to mess the rest of it up. 

Jason grabbed Tim by the hand and the two of them ran down the two flights of stairs to the street exit. Goosebumps erupted across Tim's bare arms as they burst out into the cold night and Jason quickly flagged down a taxi. Tim gave the address and they spent the ten-minute car ride making out for all they were worth. Tim fell out of the car with a giggle, as though he was drunk. Jason on the other hand shot the cab driver a grin and paid him double what he was owed before following after Tim. 

The doorman nodded to them and greeted Tim with a welcome back. Tim gave a drunken flirty grin and dragged Jason into the elevator and wrapped his arms around Jason’s neck. Jason hauled Tim up so that he was able to wrap his legs around Jason's waist and pushed him up against the wall. Jason proceeded to continue mapping out the inside of Tim's mouth with his tongue. Tim was moaning and grinding against Jason like he was going to die if Jason didn’t fuck him soon. By the time the elevator dinged and opened up to the top floor of the building, Jason was fully hard again. 

Jason carried Tim into the apartment and into the bedroom. Before Jason could reach the bed Tim wriggled out of Jason's arms. Tim shoved Jason back onto the bed and kicked his heels off before reaching under the gown and undoing whatever contraption that was keeping him contained. Tim groaned in relief as he flung the modified jock off into a corner somewhere. The dress was next to go and Jason was captivated to watch as Tim unzipped the hidden zipper and slipped the gown off, the fake breasts and scarlet pearls going with it. Tim was left naked with only the studs in his ears and the messy up-do. 

Jason scrambled to get out of his clothes and when he looked back Tim had let down his hair and was surrounded by scattered pins. Ebony locks tumbled down to his hips and Tim watched with a salacious smirk as Jason's cock twitched at the sight. It got worse as Tim stepped out of the pile of gown and pins and crawled up between Jason's legs. Tim seated himself on Jason's stomach and leaned down to give him the filthiest kiss Jason had ever experienced. This time Jason was able to tangle his fingers in Tim's hair and he couldn’t stop himself from thrusting up. Jason's cock was dripping precome and it smoothed the glide between Tim's ass cheeks. Tim moaned at the feeling and pulled back to throw his head back. Jason jerked at the sight of Tim's messed up lipstick and he let out a moan of his own.

Jason was fairly well out of it at this point. Which was why it took him longer than it should have to realize that Tim had slicked him up and had shifted once more. Jason felt his cock nudge against a puckered entrance and he jolted out of his lust induced haze.

“Woah, Tim, wait. Let me prep you first. You'll hurt yourself if I don’t, I'm not small.” Jason protested. 

Tim looked down at him with a cruel edged smile that should not have been as hot as it was. 

“Oh, didn’t I tell you, Jason?” Tim purred, “I like pain.” 

With that mind-numbing bit of information, Tim impaled himself on Jason's cock, taking him all way down to the base in one go. Tim let out a strangled scream of pain and Jason's hands immediately shot to Tim's hips to hold him steady. 

“Fuck, fuck, fuck, fuck.” Jason chanted over and over again, throwing his head back against the pillows to keep himself from thrusting into Tim. 

There was a fine line between pain and pleasure. For those who liked pain with sex that line could get blurred, but they knew their limits far better than anyone else did. If Jason moved before Tim was ready that line was going to blur very quickly into the not good realm of things. But fuck was it hard not to move. Tim was so fucking tight around Jason that it felt like he was trying to take Jason's dick off. Jason probably shouldn’t have been surprised to learn that Tim was a masochist, not after everything Jason had seen of him over the years. 

Before Jason knew he was really ready, Tim was moving. Lifting himself up and down, moaning in both pain and pleasure as he did. Jason kept his eyes locked on Tim's face because he knew if he looked down there was probably going to be blood. Jason liked causing pain and if he saw it he was going to lose it. Jason couldn’t afford to lose it during their first night. Not when they still hadn’t discussed rules and safety and all that shit. 

Tim was trembling and breathing hard, but looking fairly blissed at the same time. Tim stopped with Jason almost completely out of him and looked down. 

“It's okay, Jason. I trust you. Let go.” It was much the same as what he'd said in the stairwell, and like then, it was enough. 

Jason's control snapped. 

In an instant, he had flipped them so Tim was on his back and was slamming himself in and out of Tim. Tim screamed and arched almost painfully. His long nails digging what was no doubt bloody lines into Jason's back, but that just spurred him on. Jason leaned down and bit into Tim's chest, right above one nipple hard enough to taste blood.

“Oh! Fuck! Yes!” Tim yelled, moving his hips to meet Jason's wild thrusts.

“Fuck, Tim. I'm close.” Jason panted.

“Me too, me too.” Tim panted.

Jason picked up the pace, even more, gripping bruises into Tim's pale skin and biting more bloody marks. Jason's back felt shredded but he didn’t care. Finally, Jason found the scar on Tim's neck where Jason had tried to kill him the first time and bit down until he tasted blood. Tim arched so hard Jason was pretty sure the bird sprained something. Tim came with a scream at the same time as Jason. Jason came so hard his vision went white and he blacked out for a few seconds. 

When Jason came to he was laying on top of Tim who didn’t seem at all bothered by the fact that Jason was more or less crushing him. Jason rolled to the side and slowly pulled out of Tim. Tim winced and his breathing hitched. Jason couldn’t stop himself and looked down. That was a lot better than Jason thought it was gonna be. Jason was worried that he had torn something inside Tim, but it looked like he hadn’t. 

“You okay Tim?” Jason asked softly.

“Hmmm, aces,” Tim answered sounding as high on endorphins as he looked. 

“Come on baby, we need to get you cleaned up,” Jason said as he moved to the edge of the bed and gently hoisted Tim up into his arms. Tim winced slightly at the movement but didn’t stop Jason. 

Jason smoothly carried Tim into the attached bathroom and carefully set Tim on the shower seat before cranking the hot water. Jason turned to look at Tim who still looked high on endorphins and he figured that was probably a good thing. Jason didn’t see Tim doing too much moving around tomorrow, not with how hard Jason went at him. Jason carefully got Tim on his feet and began cleaning him up. Jason had to prompt Tim a few times about where soap was that he could use to wash the make-up off Tim's face. Jason also carefully took out the very well disguised extensions and set them aside for Tim to deal with later. 

Jason made sure to be gentle and broadcast his movements. Jason had slept with other heroes who like pain and had learned the hard way to broadcast or else get punched, or stabbed on one memorable occasion. Jason hummed a few songs he knew as he cleaned Tim up, paying special attention to Tim's lower regions. The endorphin high was clearly wearing off because Tim started resting more and more of his weight on Jason as time went on. Tim didn’t appear to be uncomfortable beyond the pain he was in from the rough fucking, which Jason was very grateful for. 

Jason finished cleaning them up and gently dried them off before picking Tim back up in his arms. Tim winced at the movement but still curled into Jason's chest. Jason gently laid them down and curled himself around Tim's much smaller frame. Tim hummed happily and wiggled himself further into Jason's chest. Jason chuckled lightly and pressed a kiss to the side of Tim's head. 

“I hope you know you're stuck with me now Babybird,” Jason whispered. 

“Good, I'd hate to have to kidnap you,” Tim replied sleepily.

“Get some sleep, we're going to need it.”

W aking up was surreal for Jason. Jason panicked slightly when he realized that Tim wasn’t in the bed with him. Fearing that Tim had left but sounds from the kitchen told Jason that Tim had merely relocated. Jason scooted to the edge of the bed and yanked on the lounge pants that were sitting on the couch at the end of the bed. Jason wandered out into the penthouse and took the time to look at everything he hadn’t paid attention to the night before. It was a beautiful place and it seemed to fit Tim perfectly. Walking into the kitchen Jason blinked.

Tim was wearing nothing but Jason's shirt from last night, moving around the kitchen as if nothing had happened last night. Sitting at the kitchen island was Stephanie Brown who gave a wolf-whistle when she saw Jason standing in the entrance to the kitchen. Tim looked over his shoulder and smiled at Jason before skipping over to Jason and kissing him lightly on the lips. 

“Morning,” Tim whispered against his lips. 

“You okay?” Jason asked. 

“Never better,” Tim said with a smile that lit up his whole face.

“I'm glad, but you should still be resting,” Jason said softly. 

“I'll be fine, Jay, but you do know what this means right?” Tim asked.

“What?”

“I totally won the bet,” Tim said with a laugh. Jason chuckled back.

“You won more than just a bet, Babybird.” 

“I certainly did.” Tim agreed, his face turning soft and his eyes filling with love.

Jason might not always think before he spoke, but sometimes it was good that he didn’t. After all, it tended to make his life interesting. 

**Notes for the Chapter:**

> Well, that's all for now folks. I am planning to write a little one-shot where Bruce and Tim dance at the Gala. As always please let me know what you think about this, I always like to hear from people.


End file.
